Thermochemiluminescence-Based Sensitive Probes: Synthesis and Photophysical Characterization of Acridine-Containing 1,2-Dioxetanes Focusing on Fluorophore Push-Pull Effects

N-substituted acridine-containing 1,2-dioxetanes have been recently proposed as thermochemiluminescence (TCL) universal labels for bioanalytical applications. The TCL properties of these compounds markedly depend on the nature of substituents of the acridine ring. In the attempt to obtain new TCL probes with improved properties and stability, the push-pull approach was adopted, in which both electron withdrawing and electron donating groups are present in the acridine moiety. The results have been useful to better understand the role of the different decorations at the acridine fluorophore in modulating the photophysical properties and the activation parameters of 1,2-dioxetane labels. Moreover, the great versatility and innovation of these molecules make them extremely attractive for bioanalytical applications, in particular as labels for immune- and gene-probe assays.